One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics

Santosh, Rangappa and Paul, Priyodip and Selvam, Mukunthan K. and Raril, Chenthattil and Krishna, Panchangam M and Manjunatha, Jamballi G and Nagaraja, Gundibasappa K. (2018) One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics. ChemistrySelect, 4 (3). pp. 990-996. ISSN 2365-6549

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Abstract

Dihydropyrimidinones (DHPMs), 4a-f and 6a-f is reported and were characterized by 1H-NMR, 13C-NMR, FT-IR and LC–MS. The synthesized compounds were evaluated for their antibacterial activity against Staphylococcus aureus (S.aureus), Bacillus subtilis (B. subtilis), Salmonella typhi (S. typhi) and Pseudomonas aeruginosa (P. aeruginosa). Among the test samples compounds, 5-(4-hydroxy-3-methoxyphenyl)-7-imino-1,3,5,6,8-pentahydropyrimido[ 4,5-d]pyrimidine-2,4-dione (6 c) and 5-(4- hydroxy-3,5-dimethoxyphenyl)-1,3-N,N-dimethyl-7-thioxo-5,6,8- trihydropyrimido[4,5-d]pyrimidine-2,4-dione (4 d) were more potent against S. aureus and B. subtilis. Whereas 5-(4-hydroxy-3- methoxyphenyl)-1,3-N,N-dimethyl-5,6,8-trihydropyrimido[4,5-d] pyrimidine-2,4,7-trione (6 e) and 5-(4-hydroxy-3,5-dimethoxyphenyl)- 1,3-N,N-dimethyl-5,6,8-trihydropyrimido[4,5-d]pyrimidine- 2,4,7-trione (4 e) showed good inhibition against S. typhi and P. aeruginosa which were well supported by computational interaction and DNA binding studies. Compound 5-(4-hydroxy- 3,5-dimethoxyphenyl)-7-imino-1,3,5,6,8-pentahydropyrimido [4,5-d]pyrimidine-2,4,7-trione (4 c) exhibited potent scavenging activity with IC50 of 8.30 mg/ml. Furthermore, Cyclic Voltammetric analysis disclosed that 5-(4-hydroxy-3,5-dimethoxyphenyl)- 7-thioxo-1,3,5,6,8-pentahydropyrimido[4,5-d]pyrimidine-2,4- dione (4 a), 5-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,5,6,8-pentahydropyrimido[ 4,5-d]pyrimidine-2,4,7-trione (4 b), 4c, 6d, 6e, and 6f showed redox behavior

Item Type: Article
Uncontrolled Keywords: Antibacterial,Antioxidant,Biginelli Pyrimidines,Cyclic Voltammetry DNA Binding Studies Molecular Doc
Subjects: Engineering > MIT Manipal > Biotechnology
Depositing User: MIT Library
Date Deposited: 30 Jan 2019 10:58
Last Modified: 30 Jan 2019 10:58
URI: http://eprints.manipal.edu/id/eprint/153118

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